反应 #50672

反应方程式

2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

oxalyl chloride

pyrrole-2-carboxylic acid

tin (IV) chloride

→

product

收率 69.2%

2-[2-(1H-Pyrrol-2-ylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

收率 69.2%

溶剂

water

DCM

反应条件

后处理

1. 1
   温度The reaction mixture was heated
2. 2
   温度under reflux for 1 hour
3. 3
   workup.STIRRINGby stirring at -10° C. for additional 30 minutes
4. 4
   萃取extracted with DCM
5. 5
   洗涤The combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid
6. 6
   干燥The dried (magnesium sulfate) organic phase
7. 7
   过滤was filtered
8. 8
   其他evaporated in vacuo
9. 9
   其他The residue was triturated with DCM

实验过程

To a suspension of pyrrole-2-carboxylic acid (5.55 g) in 500 ml of DCM was added oxalyl chloride (8.7). The reaction mixture was heated under reflux for 1 hour, cooled to -10° C., and tin (IV) chloride (5.85 ml) was added. After stirring the mixture at -10° C. for 30 minutes, 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (10.6 g) was added in four portions over a period of 30 minutes, followed by stirring at -10° C. for additional 30 minutes. The reaction mixture was then poured into 500 ml of water and extracted with DCM. The combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid, and finally with water. The dried (magnesium sulfate) organic phase was filtered and evaporated in vacuo. The residue was triturated with DCM, affording the product as a powder (10.55 g), mp 204°-206° C.

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